To countless admirers in the '80s, she was Claire, the popular princess with the infamous hands-free lipstick-application technique. Or Sam, the birthday-girl-next-door who won the heart of the ultimate BMOC, Jake Ryan. Or Andie, the original Etsy girl who made it cool to wear a deconstructed DIY dress to the prom. Or even little Molly Parker, the plucky boarding-school student who plucked a ukulele on "The Facts Of Life." But to most, she was just Molly Ringwald. She was that special girl who captured the hearts of America's Blanes and Duckies alike--"your former teenage crush," according to the bio on her own Twitter page.

Since Molly's teen dramedy days, she's kept busy writing both fiction and non-fiction; acting in film, television, and theater; and parenting her three children. But now she has launched a new venture: a jazz music career, with an album of standards from the Great American Songbook, Except Sometimes. This may seem like a major stylistic departure for the former new wave girl who once memorably danced in slouchy boots in the Shermer High School detention center, but the album does offer one touching nod to Molly's '80s past: a cocktail-jazz remake of Simple Minds' "Don't You (Forget About Me)," which, of course, was the theme song to perhaps the most famous film she made with legendary late director John Hughes, The Breakfast Club.

"When I recorded the album, it was not that long after John passed away, so he was still on my mind a lot, and I kind of wanted to pay tribute to him," Molly recalls, when asked why she chose to musically revisit her teen-movie past. (She and John didn't speak for years, though they reconnected via letter before his 2009 death.) "And I also wanted to sort of integrate who I was into who I am now. I can't really distance myself from that [era], nor do I really think that I need to. I feel like by reimagining and singing the song in a completely different way as an adult, incorporating what I'm interested in now, I'm making a statement. I'm not a different person, I've just evolved. And I think the treatment of the song kind of expresses that in a nice way."

While Molly grew up in a musical family, she credits John Hughes, a true pioneer in the genre of cool film soundtracks, with expanding her musical horizons. "Music was incredibly important to John, and he had an amazing, amazing record collection," she remembers fondly. "I didn't really know the Beatles because I grew up with jazz, so he sort of introduced me to them, album by album. I really remember that a lot. And also a lot of the artists that ended up on his soundtracks: Echo & The Bunnymen, the Smiths. He made me the most incredible mixtapes, which it just kills me that I don't still have! I've moved so many times and I don't know what happened to them; my sister probably took them at some point, since she was always stealing my mixtapes. [EDITOR'S NOTE TO MOLLY: CALL UP YOUR SISTER AND GET THOSE TAPES BACK! NOW!] John and I made a lot of mixtapes for each other; I don't think he had heard [the Psychedelic Furs'] 'Pretty In Pink' until I played it for him."

Ah, Pretty In Pink--the most rock 'n' roll of all Ringwald/Hughes film collaborations, not just because it took its title from that killer Furs track, but because several of its pivotal scenes took place in a supercool indie record store, TRAX. Retail hangouts like TRAX sadly barely even exist anymore, but the coming-of-age film has nonetheless aged very well. "Thanks, I just showed the movie to my 9-year-old for the first time a couple days ago," chuckles Molly. "But she was Team Ducky. She said after the movie, 'I'm sorry, Mom, but Ducky's my favorite character.'"

There are no doubt many Pretty In Pink fans who wish that the film's original ending--in which Molly's character Andie would've wound up happily ever after with her quirky platonic pal Ducky (played by Jon Cryer), instead of with popular rich kid Blane (Andrew McCarthy)--had made it to the big screen. And Molly jokingly says that mythical footage "probably exists in a vault on the John Hughes estate." But she doesn't necessarily agree with those fans, or with her daughter; she's Team Blane in this case. "That ending totally didn't work. If you have a Cinderella story, which essentially it is...she wasn't in love with Ducky. He was just her best friend. Ducky was kind of based on my [real-life] best friend, who I'm still best friends with; that's where John pulled it from. It was kind of like this friendship where they'd known each other forever, best friends...and best friends don't necessarily end up together. And I have a theory that I think Ducky is gay--I talk about that ad nauseam, but a lot of people vehemently disagree with me!"

Okay, so that issue is still very much up for debate. But, back to the music: One thing that's not up for debate is the fact that Molly can actually sing. While more casual types may be skeptical of her decision to record jazz--or of any actor's decision to record any sort of album--Molly actually has real jazz cred and musical experience. Her father, Bob Ringwald, is a jazz pianist, and she began sitting in with his Fulton Street Jazz Band when she was only 3 years old. Except Sometimes isn't even technically her first jazz record, since she released a Dixieland jazz collection with her father's group called I Wanna Be Loved By You when she was 6 years old. "There were probably about a thousand copies printed, and you could get them on eBay if you wanted to pay a lot of money," she laughs, most likely blissfully unaware that the entire (adorable) album is available for streaming online. Years later, as she returns to music, Molly admits, "I'm sure that there are some people who are doubters," but adds, "Most people that really know me know I have a jazz background. I feel like I have jazz in my DNA."

So why did it take so long--almost four decades--for the grown-up Molly to record a follow-up album? "I think it was just the right time. I've wanted to put a jazz group together for a while, and it just kind of happened. When I met my pianist, my collaborator, who arranges the music, Peter Smith, we started working together and developed a sort of simpatico relationship. It just felt right. I didn't even know necessarily that I was going to record an album, but I was really enjoying the work we were doing and I wanted to have a record of it, and it all sort of happened very organically."

As totally awesome as it may have been for Molly and her band to do an entire album of jazzified '80s covers--especially a cover of "Pretty In Pink," obviously--when she entered the studio she didn't entertain that idea, instead sticking to timeless crooner classics like "The Very Thought Of You," "I'll Take Romance," and "I Get Along Without You Very Well" on Except Sometimes. "I did the one ['80s] song for the reasons that I already mentioned, but to do a whole album of just '80s music I think would be a little much--because, like I said, I don't live in the past," says Molly, who has also written her own songs and doesn't rule out recording an album of originals in the future. "But there's a lot of music that I love. I went to go hear Elvis Costello, and he did a jazz version of 'Watching The Detectives' that was just amazing. So I think if I did anybody's music [from the '80s era], it would probably be him."